‘Gilmore Girls’: 4 of Rory Gilmore’s Cringiest Moments
Gilmore Girls has managed to remain a culturally relevant touchstone decades after its initial release, even producing a Netflix revival that revisited the characters years after the original conclusion. There’s no doubt that the series remains beloved by many, but that doesn’t mean everything has aged gracefully.
In particular, fans have pointed to some truly cringy behavior from one of the show’s titular “girls.” Rory Gilmore — the golden child and darling of Star’s Hollow — doesn’t look quite so rosy with the addition of hindsight.
Here are four of Rory Gilmore’s cringiest moments.
Rory dressed up like a ’50s housewife to impress Dean (Season 1, Episode 14)
Early in the show, Rory was quite smitten with Dean. From the beginning of their relationship, their differences were highlighted as a point of contention. These would eventually become fuel for a fire that still has fans divided on which of Rory’s suitors was right for her.
But all of that was in the future for Season One Rory, who just wanted to make a good impression on her beau, a simple man who expressed a nostalgic appreciation for gender roles from a simpler time. Rory decides to lean into this preference and goes full “Donna Reed” by putting on a 1950s-style dress and making dinner like a good little housewife.
The moment was played off as light-hearted puppy love, but considering Rory’s seeming commitment to equal treatment of women, it definitely feels cringey in retrospect.
Rory misunderstands William’s story (Season 4, Episode 11)
When Carly Simon sang the line “you’re so vain, you probably think this song is about you,” she probably didn’t have Rory Gilmore in mind, but the sentiment fits. Years later, Rory has moved on to become a promising Yale student, but her love life is in disarray.
When she gets brave enough to ask a cute acquaintance named William on a date, she’s mildly humiliated by a rejection. This minor moment turns into a full-blown issue when Rory overhears the young man gossiping about an obsessed girl who won’t stop stalking him.
Assuming that William is gossiping about her, Rory calls him out for his hyperbole in front of his friends in the dining hall. However, William wasn’t actually talking about Rory. The moment is painful to watch!
Rory badmouths Lindsay and gets caught (Season 4, Episode 18)
What goes around comes around, and Rory’s back in Star’s Hollow, once again pining for Dean — but now he’s married. Ironically, Dean is now living out that Donna Reed dream he always wanted, but it isn’t going so well. His new wife Lindsay has chosen to be a homemaker, but Dean’s paycheck isn’t covering their expenses as well as they’d hoped.
Dean can’t go to college because he has responsibilities at home and bills to pay. Rory is complaining about all of this to Lane in the middle of the grocery store. She makes no effort to be discreet, and Lindsay overhears everything she says. Humiliating!
Rory blames Lindsay for Dean’s cheating (Season 4, Episode 22)
Eventually, the sparks between Rory and Dean catch fire, and the two of them end up sleeping together while Dean is still married. When Lorelai confronts her daughter about this troubling turn of events, Rory takes virtually no responsibility for knowingly sleeping with a married man.
In fact, she tries to toss the blame on the wronged wife! Rory insists on calling him “my Dean” before essentially blaming Lindsay for more or less forcing Dean to cheat. “It’s not working out between them,” she reasons away her guilt. “They’re not happy.”
As Lorelai presses, Rory digs in: “She’s not good for him, OK? She lets him quit school and work himself to death.” Lorelai cuts her off and tells her she can’t be the type of woman who attacks the victim. The audience cringing at home likely agrees!
